Literature DB >> 32359086

Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals.

Haibo Mei1, Jianlin Han1, Sarah White2, Daniel J Graham2, Kunisuke Izawa3, Tatsunori Sato3, Santos Fustero4, Nicholas A Meanwell5, Vadim A Soloshonok6,7.   

Abstract

Structural analysis of modern pharmaceutical practices allows for the identification of two rapidly growing trends: the introduction of tailor-made amino acids and the exploitation of fluorinated motifs. Curiously, the former represents one of the most ubiquitous classes of naturally occurring compounds, whereas the latter is the most xenobiotic and comprised virtually entirely of man-made derivatives. Herein, 39 selected compounds, featuring both of these traits in the same molecule, are profiled. The total synthesis, source of the corresponding amino acids and fluorinated residues, and medicinal chemistry aspects and biological properties of the molecules are discussed.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords:  amino acids; cancer; drug discovery; fluorine substitution; fluorine-containing drugs

Mesh:

Substances:

Year:  2020        PMID: 32359086     DOI: 10.1002/chem.202000617

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  11 in total

1.  Janus All-Cis 2,3,4,5,6-Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry.

Authors:  Joshua L Clark; Rifahath M Neyyappadath; Cihang Yu; Alexandra M Z Slawin; David B Cordes; David O'Hagan
Journal:  Chemistry       Date:  2021-10-06       Impact factor: 5.020

Review 2.  Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives.

Authors:  Jianlin Han; Jorge Escorihuela; Santos Fustero; Aitor Landa; Vadim A Soloshonok; Alexander Sorochinsky
Journal:  Molecules       Date:  2022-06-13       Impact factor: 4.927

3.  Asymmetric Mannich reactions of (S)-N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimines with yne nucleophiles.

Authors:  Ziyi Li; Li Wang; Yunqi Huang; Haibo Mei; Hiroyuki Konno; Hiroki Moriwaki; Vadim A Soloshonok; Jianlin Han
Journal:  Beilstein J Org Chem       Date:  2020-10-29       Impact factor: 2.883

Review 4.  Recent Advances on the Halo- and Cyano-Trifluoromethylation of Alkenes and Alkynes.

Authors:  Bo Fu; Jorge Escorihuela; Jianlin Han; Santos Fustero; Pablo Barrio; Mikiko Sodeoka; Shintaro Kawamura; Alexander Sorochinsky; Vadim A Soloshonok
Journal:  Molecules       Date:  2021-11-28       Impact factor: 4.411

Review 5.  Fluorinated triazoles as privileged potential candidates in drug development-focusing on their biological and pharmaceutical properties.

Authors:  Ihsan Ullah; Muhammad Ilyas; Muhammad Omer; Muhammad Alamzeb; Muhammad Sohail
Journal:  Front Chem       Date:  2022-08-09       Impact factor: 5.545

Review 6.  The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine.

Authors:  Qian Wang; Jianlin Han; Alexander Sorochinsky; Aitor Landa; Greg Butler; Vadim A Soloshonok
Journal:  Pharmaceuticals (Basel)       Date:  2022-08-14

7.  Selectively Fluorinated Citronellol Analogues Support a Hydrogen Bonding Donor Interaction with the Human OR1A1 Olfactory Receptor.

Authors:  Mengfan He; Weihong Liu; Chen Zhang; Yingjian Liu; Hanyi Zhuang; David O'Hagan
Journal:  Org Lett       Date:  2022-06-10       Impact factor: 6.072

Review 8.  Chemical Aspects of Human and Environmental Overload with Fluorine.

Authors:  Jianlin Han; Loránd Kiss; Haibo Mei; Attila Márió Remete; Maja Ponikvar-Svet; Daniel Mark Sedgwick; Raquel Roman; Santos Fustero; Hiroki Moriwaki; Vadim A Soloshonok
Journal:  Chem Rev       Date:  2021-03-16       Impact factor: 60.622

Review 9.  Recommended Tests for the Self-Disproportionation of Enantiomers (SDE) to Ensure Accurate Reporting of the Stereochemical Outcome of Enantioselective Reactions.

Authors:  Jianlin Han; Alicja Wzorek; Karel D Klika; Vadim A Soloshonok
Journal:  Molecules       Date:  2021-05-07       Impact factor: 4.411

Review 10.  Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature.

Authors:  Yupiao Zou; Jianlin Han; Ashot S Saghyan; Anna F Mkrtchyan; Hiroyuki Konno; Hiroki Moriwaki; Kunisuke Izawa; Vadim A Soloshonok
Journal:  Molecules       Date:  2020-06-12       Impact factor: 4.411

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